1,6-dinitro-5H,10H-diimidazo<1,5-a:1',5'-d>pyrazine-5,10-dione | 78595-40-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并[1,5-a]吡嗪
• 英文名称: 1,6-dinitro-5H,10H-diimidazo<1,5-a:1',5'-d>pyrazine-5,10-dione
• 英文别名: 1,6-dinitro-5H,10H-diimidazo<1,5-a;1',5'-d>pyrazine-5,10-dione；1,6-dinitro-5H,10H-diimidazo<1,5-a:1'-d>pyrazine-5,10-dione；1,6-dinitro-5H,10H-diimidazo[1,5-a:1',5'-d]pyrazine-5,10-dione；4,10-dinitro-1,5,7,11-tetrazatricyclo[7.3.0.03,7]dodeca-3,5,9,11-tetraene-2,8-dione
• CAS: 78595-40-1
• 化学式: C₈H₂N₆O₆
• 分子量: 278.14
• InChiKey: ZOQYALHHEQSHQA-UHFFFAOYSA-N

物化性质

• 熔点：
  249-251 °C
• 沸点：
  835.7±75.0 °C(Predicted)
• 密度：
  2.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.04
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  155.02
• 氢给体数：
  0.0
• 氢受体数：
  10.0

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1,6-dinitro-5H,10H-diimidazo<1,5-a:1',5'-d>pyrazine-5,10-dione 、 6-amino-4-[(3-chlorophenyl)amino]quinazoline 在 铁粉 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 乙醇 、 水 为溶剂， 反应 49.0h， 生成 JDF04R
  参考文献：
  名称：

  IMIDAZOTETRAZINONE-BASED COMBI-MOLECULES

  摘要：

  这里描述了一系列展示抗肿瘤活性的新化学试剂。这些新化学试剂表现出双重抗肿瘤作用方式：阻断表皮生长因子受体（EGFR）介导的信号传导，并通过烷基化损害DNA。

  公开号：

  US20120283280A1
• 作为产物：
  描述：

  4-硝基-1H-咪唑-5-羧酸 在 氯化亚砜 作用下， 反应 2.0h， 生成 1,6-dinitro-5H,10H-diimidazo<1,5-a:1',5'-d>pyrazine-5,10-dione
  参考文献：
  名称：

  IMIDAZOTETRAZINONE-BASED COMBI-MOLECULES

  摘要：

  这里描述了一系列展示抗肿瘤活性的新化学试剂。这些新化学试剂表现出双重抗肿瘤作用方式：阻断表皮生长因子受体（EGFR）介导的信号传导，并通过烷基化损害DNA。

  公开号：

  US20120283280A1

文献信息

• Tetrazine derivatives
  申请人：Cancer Research Campaign Technology Limited

  公开号：US05260291A1

  公开（公告）日：1993-11-09

  [ 3H]-Imidazo[ 5,1-d] -1,2,3,5-tetrazin-4-one derivatives of the formula: ##STR1## wherein R.sup.1 represents hydrogen, or an alkyl, alkenyl or alkynyl group containing up to 6 carbon atoms, each such group being unsubstituted or substituted by from one to three substituents selected from halogen atoms, alkoxy, alkylthio, alkylsulphinyl and alkylsulphonyl groups containing up to 4 carbon atoms, and optionally substituted phenyl groups, or R.sup.1 represents a cycloalkyl group containing from 3 to 8 carbon atoms, and R.sup.2 represents a carbamoyl group optionally N-substituted by one or two groups selected ftom alkyl and alkenyl groups containing up to 4 carbon atoms, and cycloalkyl groups containing 3 to 8 carbon atoms, are new therapeutically useful compounds possessing antineoplastic and immunomodulatory activity.

  该公式的[3H]-Imidazo[5,1-d]-1,2,3,5-四唑-4-酮衍生物：其中R1代表氢，或者是含有最多6个碳原子的烷基，烯基或炔基，每个这样的基团未被取代或被从卤素原子，烷氧基，烷硫基，烷基亚磺酰基和烷基磺酰基中选择的1到3个取代基取代，这些取代基含有最多4个碳原子，并且可以是取代的苯基，或R1代表含有3到8个碳原子的环烷基，R2代表一个氨基甲酰基团，该氨基甲酰基团可以被一个或两个选择自含有最多4个碳原子的烷基和烯基团和含有3到8个碳原子的环烷基的基团取代，是新的具有抗肿瘤和免疫调节活性的治疗上有用的化合物。
• Antitumor imidazotetrazines. 14. Synthesis and antitumor activity of 6- and 8-substituted imidazo[5,1-d]-1,2,3,5-tetrazinones and 8-substituted pyrazolo[5,1-d]-1,2,3,5-tetrazinones
  作者：Edward Lunt、Christopher G. Newton、Christopher Smith、Graham P. Stevens、Malcolm F. G. Stevens、Colin G. Straw、Roger J. A. Walsh、Peter J. Warren、Christian Fizames

  DOI：10.1021/jm00385a018

  日期：1987.2

  The systematic variation of the potent antitumor agent mitozolomide (1) is extended to cover alteration of substituents at positions 6 and 8 and to change the imidazo[5,1-d]-1,2,3,5-tetrazinone (1) skeleton to the isomeric pyrazolo-[5,1-d]-1,2,3,5-tetrazinone (17) skeleton. The series of eight 6-alkyl and 6-aralkyl derivatives of 1 showed optimal antitumor activity when the group was small or linear, but activity diminished as size and branching of this substituent increased. This may reflect altered transport characteristics, or failure of the enlarged derivatives to fit a binding site, or possibly a reduced tendency for the derivatives having bulky groups at position 6 to hydrolytically generate the putatively active triazenes (21). Testing of 14 derivatives of 1 differently substituted at position 8 revealed a complex structure-activity relationship, with good antitumor activity obtained for carbamoyl and sulfamoyl groups bearing small substituents. The 8-methylsulfonyl compound had noteworthy activity, but the 8-cyano, 8-nitro, and 8-phenyl derivatives were devoid of useful antitumor activity in these tests. From the limited number of pyrazolotetrazinones (17) reported here, it is suggested that the same conclusions as regards activity also hold true for this ring system.
• Antitumor imidazotetrazines. 20. Preparation of the 8-acid derivative of mitozolomide and its utility in the preparation of active antitumor agents
  作者：K. R. Horspool、M. F. G. Stevens、Christopher G. Newton、E. Lunt、R. J. A. Walsh、B. L. Pedgrift、G. U. Baig、F. Lavelle、C. Fizames

  DOI：10.1021/jm00167a018

  日期：1990.5

  The preparation of 3-(2-chlorethyl)-4-oxo-3H-imidazo[5,1-d]-1,2,3,5- tetrazine-8-carboxylic acid, a key derivative of mitozolomide in our exploration of the structure-activity relationships of this class of antitumor agents, is described. The facile conversion to the 8-carbonyl chloride gave a derivative that reacted preferentially with nucleophiles at the 8-position rather than at the reactive 4-oxo group, allowing the preparation of a wide range of ester, thioester, amide (including an amide derived from an amino acid), hydroxamic acid, hydrazide and sulfoximide, azide and diazoacetyl derivatives. The in vivo activity is presented of a range of these compounds against TLX5 lymphoma and L1210 leukemia cell lines.
• Clark; Deans; Stevens, Journal of Medicinal Chemistry, 1995, vol. 38, # 9, p. 1493 - 1504
  作者：Clark、Deans、Stevens、Tisdale、Wheelhouse、Denny、Hartley

  DOI：——

  日期：——
• Novel approach to the synthesis of a xanthine homolog
  作者：�. I. Ivanov、G. D. Kalayanov、I. M. Yaroshchenko

  DOI：10.1007/bf00509728

  日期：1990.7